m-Chloroperbenzoic acid → SK&F 105809
Reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH2:22][CH2:21][CH2:20][N:12]3[C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]3[CH2:22][CH2:21][CH2:20][N:12]3[C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:7][CH:8]=1)=[O:31]Participants
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of 5.0 g (16.3 mmoles) of 2-(4-methylthiophenyl)-3-(4-pyridyl)-6,7-dihydro [5H]-pyrrolo[1,2 a]imidazole of Example 3 dissolved in 75 ml of chloroform, chilled in an ice bath, was added dropwise a solution of 3.30 g (16.3 mmoles) of 85% 3-chloroperbenzoic acid in chloroform. After stirring at 25° C. overnight, the reaction mixture was washed with 5% sodium carbonate, dried over anhydrous potassium carbonate, and stripped in vacuo. The residue was flash chromatographed on silica eluting with 5 to 10% methanol in methylene chloride: 2-propanol (9:1). The solvent was removed in vacuo and the residue recrystallized from ethyl acetate to give the desired titled compound, mp 163.5-165.5° C. 1H NMR (360 MHz, CDCl3) δ8.62 (2H,d), 7.68 (2H,d), 7.57 (2H,d), 7 25 (2H,d), 4.05 (2H,t), 3.02 (2H,t), 2.72 (s) superimposed upon 2.69 (m) (5H total). Mass Spec. (CI) (M+H) 324 (MW=323).
Workup
- temperaturechilled in an ice bath
- washthe reaction mixture was washed with 5% sodium carbonate
- dry with materialdried over anhydrous potassium carbonate
- customchromatographed on silica eluting with 5 to 10% methanol in methylene chloride: 2-propanol (9:1)
- customThe solvent was removed in vacuo
- customthe residue recrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-4e8efd4db4d74412a1744a6fd34bcdab
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05002941
Reaction notes
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